Bennington Holidays

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Top Flight + Hotel Deals in Bennington

Price found within the past 48 hours. Click for updated prices.
Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

3 out of 5
per person
8 May - 11 May
found 3 hours ago
Return flight included
Louisville (SDF) to Albany (ALB)
9.2/10 Wonderful! (506 reviews)
Have been coming to Bentley for years- love the ski on/ski off for JiminyPeak. The staff is very nice, very welcoming- a definite keeper!

Reviewed on 1 Feb 2025

The Manchester View

The Manchester View

2.5 out of 5
per person
8 May - 11 May
found 3 hours ago
Return flight included
Louisville (SDF) to Albany (ALB)
9.4/10 Exceptional! (687 reviews)
Nice and cozy room. Property is beautiful. Close to all the shopping and restaurants.

Reviewed on 16 Mar 2025

The Little Lion

The Little Lion

3 out of 5
per person
8 May - 11 May
found 3 hours ago
Return flight included
Louisville (SDF) to Albany (ALB)
8.8/10 Excellent! (475 reviews)
Easy check in. No disturbances. Cute rooms. Disappointed there was no availability for my last trip to GB because I would have loved to stay here one last time.

Reviewed on 20 Feb 2025

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
per person
8 May - 11 May
found 3 hours ago
Return flight included
Louisville (SDF) to Albany (ALB)
8.6/10 Excellent! (1,786 reviews)
Very nice accomodations, more like a mini apartment than a motel room.

Reviewed on 19 Mar 2025

Hotel On North

Hotel On North

3.5 out of 5
per person
8 May - 11 May
found 3 hours ago
Return flight included
Louisville (SDF) to Albany (ALB)
9.6/10 Exceptional! (692 reviews)
Nice stay at the property, the rooms are huge… the wooden floors do creek a bit so you can hear people walking around but if you don’t mind that, it’s a pretty cool hotel, nicely decorated.

Reviewed on 24 Mar 2025

Top hotels in Bennington

Hotel Vervana, Trademark Collection by Wyndham
Hotel Vervana, Trademark Collection by Wyndham
2.5 out of 5
141 West Main Street, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is €110 per night from 1 Apr to 2 Apr
€110
includes taxes & fees
1 Apr - 2 Apr
8.2/10 Very Good! (999 reviews)
"Property was very hard to find. There is a big sign by the road but then nothing else. It’s hidden in the back behind another building. It looks like it could be an apartment complex without a sign."

Reviewed on 9 Mar 2025

Hotel Vervana, Trademark Collection by Wyndham
Hampton Inn Bennington
Hampton Inn Bennington
2.5 out of 5
51 Hannaford Square, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is €136 per night from 6 Apr to 7 Apr
€136
includes taxes & fees
6 Apr - 7 Apr
8.6/10 Excellent! (966 reviews)
"Staff was very friendly and helpful. Good breakfast, clean room & bathroom. Heater kind of loud & I think the price per night was very high. Also difficult to hear others checking in with a much lower rate. March is March....the room shouldn't be more or less depending on booking time frame."

Reviewed on 14 Mar 2025

Hampton Inn Bennington
Best Western Bennington
Best Western Bennington
2.5 out of 5
220 Northside Drive, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is €107 per night from 31 Mar to 1 Apr
€107
includes taxes & fees
31 Mar - 1 Apr
7.6/10 Good! (825 reviews)
"Breakfast was awesome and the morning staff were fantastic. Room was clean. Good quick stay."

Reviewed on 25 Feb 2025

Best Western Bennington
See all 751 properties in Bennington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Bennington holiday package cost?
Offering excellent value package deals from €336 on Expedia, you’ll be thrilled with how little a holiday to Bennington costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Bennington?
You can generally find lower prices and greater availability in January, March and November. Browse our cheap Bennington holiday packages and you could land some great off-season discounts.
How many days is enough for Bennington?
With about 2 days, you’ll have plenty of time to experience popular neighbourhoods like Old Bennington and South Shaftsbury during your Bennington holiday. Remember to also add Norman Rockwell Exhibition and Robert Frost Stone House Museum to your list of must-sees. Looking for more adventures? Consider venturing outside of Bennington on day trips and tours.
Is it worth booking a holiday package to Bennington?
Bennington is a good holiday destination with attractions like Bennington Battle Monument among the many things to keep you busy. Whether you’re heading away with the family or getting away with friends, a Bennington holiday promises a good time for everyone.
How to find the best Bennington package deals?
Finding a cheap Bennington package deal is a cinch with Expedia. After you’ve entered your destination and trip dates under our “Packages” tab, set your maximum budget, apply a few filters and see what’s available. You can tailor your search by “Amenities,” “Property type,” “Traveller experience” and more. Order the results by “Price: low to high” to view the most affordable Bennington package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Bennington holiday as a package?
You can enjoy significant savings on your Bennington getaway by booking a personalised holiday package. Click on the “Package” heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Bennington?
Score amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Bennington adventure.
How to plan a trip to Bennington?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to escape to Bennington.
  2. Plan your budget wisely: As well as the price of your stay, you should factor in other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that may arise during your trip to Bennington.
  3. Decide how long to go for: Now that you’re more familiar with Bennington, you can figure out the right length of your break. Create a draft plan and give yourself enough time for all the things you want to do.
  4. Combine your accommodation and airfare: After you’ve nailed down your travel dates and duration, book the ideal Bennington holiday package for you.

Popular places to visit

Hemmings Motor News Car Lover's Convenience Store & Vehicle Display

You can spend an afternoon exploring the galleries in Hemmings Motor News Car Lover's Convenience Store & Vehicle Display during your travels in Bennington. While you're here, you can savour the cosy cafes.

Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.